Potassium Phosphate, Tribasic → 6-(4-Hydroxy-2-methyl-phenyl)-1,2-dimethyl-1H-indole-3-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A flask containing a mixture of 6-chloro-1,2-dimethyl-1H-indole-3-carboxylic acid methyl ester (1.60 g, 6.73 mmol), 3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (3.15 g, 13.5 mmol), aqueous tribasic potassium phosphate (1.27 M, 9.0 mL, 11 mmol), tricyclohexylphosphine (53 mg, 0.19 mmol) and tris(dibenzylideneacetone)dipalladium (0) (73 mg, 0.080 mmol) and dioxane (22 mL) is evacuated and filled with nitrogen several times. The reaction mixture is heated to 100° C. for 18 h. The mixture is allowed to cool and is filtered thru celite, washing with ethyl acetate. The filtrate is concentrated and partitioned with 1 N HCl and ethyl acetate. The ethyl acetate layer is washed with brine, dried over MgSO4 and concentrated. The residue is triturated in THF-heptane to provide 1.83 g (88%) of the title compound as a white solid. MS m/e 310.0 (M+1).

Provenance & Evidence